Jay Z And David Letterman Had An Interesting Convo About Believing They’re Better Men Now After Cheating On Their Wives

April 6, 2018  |  

That headline probably sounded shadier than it was intended to be, but it’s also accurate. Jay Z and David Letterman did have an interesting conversation about cheating on their wives and, like many of us who still can’t look at Jay without thinking about what he did to Bey (I don’t think any of us were as invested in David Letterman’s shenanigans), neither celebrity is completely sure they are a better man today than they were in the past. But they’re both trying.

Jay Z appeared on David Letterman’s Netflix show, My Next Guest Needs No Introduction, and while the fellas chatted about everything from politics and fatherhood to music and Jay’s mother’s coming out, it was Letterman who took the opportunity to do something we rarely see men do: talk publicly about how they f-cked up.

Speaking on his own transgressions when, in 2009, he was blackmailed for sleeping with members of his Late Show staff, Letterman said:

“I did something that I had no business doing, and I regret it, and since then I have tried to acknowledge that mistake and be a better person. You can only stop behavior that was hurting people and apologize for it and try to continue to be a better person.

“I like to think — and maybe this is flattery that I can’t afford — that, I’m a better person, not the person that caused so much pain for so many people. But, at the time, the pain that I caused myself was the fear that I had blown up my family, that I was gonna be in a situation where I would see my son every two weeks, my wife would be dating Scott, the dentist from New Jersey.

“I would go to therapy, and I would talk to people about this situation and they would tell me various things to just get me out of the office, but I never talked to a person who had had been in that situation,” he added. “I’m wondering if this rings a bell with you, the pain of ‘Have I done something now to blow up my family?'”

It absolutely did, as Jay Z told Letterman in response:

“Yeah, for a lot of us we don’t have — especially where I grew up and men in general — we don’t have emotional queues from when we’re young. Our emotional queue is ‘Be a man, stand-up, don’t cry.’

“The idea of I will never, can’t see it coming down my eyes, but I’ve gotta make the song cry, is my way of saying I want to cry, I want to be open, I want to have the emotional tools that it takes to keep my family together,” the rapper said referencing his 2001 track, Song Cry. 

“Much like you, I have a beautiful wife who is understanding and knew that I’m not the worst of what I’ve done,” Jay Z continued. “We did the hard work of going to therapy, and really we love each other so, we really put in the work, and for years. This music that I’m making now is a result of things that happened already and, like you, I like to believe that we’re in a better place today but still working and communicating and growing.

“I’m proud of the father and the husband that I am today because of all the work that was done.”

Like Beyoncé, Letterman’s wife, Regina Lasko, chose to stay with him after he confessed to sleeping with several of his female staffers. Letterman and Lasko started dating in 1986 and finally wed in 2009. The couple has a son, Harry, who was born in 2003. Jay Z and Beyoncé just celebrated their 10th wedding anniversary Wednesday.

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